Potassium Carbonate → 1-(6-Chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone

HRID 2057756Notes

Reaction equation

HRID 2057756 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>C(#N)C>[Cl:8][C:4]1[N:3]=[C:2]([O:1][CH2:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 1785160256-chloropyridin-2-ol

Product 1

HCID 204937271-(6-Chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanoneYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 400 g (3.09 moles) of 2-hydroxy-6-chloropyridine and 450 g (3.26 moles) potassium carbonate in 3000 ml acetonitrile was added 551 g (3.08 moles) 1-bromo-3,3-dimethyl-2-butanone. The reaction mixture was stirred at 45°-50° C. for 1.5 hours and then filtered. The solids were washed several times with acetonitrile, the filtrate dried (MgSO4) and the solvent evaporated. Crystallization of the residue from pentane gave 610 g (87% yield) of 1-(6-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone. A second recrystallization from pentane gave product melting at 43°-44.5° C.

Workup

  1. filtrationfiltered
  2. washThe solids were washed several times with acetonitrile
  3. dry with materialthe filtrate dried (MgSO4)
  4. customthe solvent evaporated
  5. customCrystallization of the residue from pentane

Sources & evidence

ORD record
ord-a0fbfd1422084202b1f3b7c78971bff7
Source dataset
uspto-grants-1980_07
Patent number
US04212869

Reaction notes

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